I absolutely loathe software estimates. They put engineers in a damned if you do, damned if you don't scenario that isn't even in their full control anyway. I think this is one of the things that Shape Up got the most absolutely correct - inverting the relationship between an estimate and time. We've been asking the wrong question all along: Instead of asking "how long will X take?" you should be asking "How long do…
Granted, this whole thing works for me as I happen to thrive under pressure.